Azo dye and process of making same.



Minn STATES Patented March 8, 1904,

PATENT OFFICE.

FABRIK.

LUDVVIGSHAFEN-ON-THE- TO 'BADISCHE ANILIN AND SODA AZO aw; AND Pnocsss OF MAKING SAME.

SPECIFICATION forming art of Letters Patent No. 754,315, dated March 8,1904.

Application filed March 19,

To all whom 'it may concern.-

. dye-bath bisulfite of soda solution.

- hydrochloric acid or phenylenediamin with Be it known that W6,PAUL JULIUS and ERNST FUSSENEGGER,bO'tl1 doctors of philosophy,subjects of the Emperor of Austria-Hungary, residing at Ludwigshafen-on-the-Rhine, in the Empire of Germany, have invented new and useful Improvements'in Azo'Coloring-Matter and Processes of Producing Same, of which the following is a specification.

We have discovered that by treating oncmolecular proportion of a monoalkyl paraat iiast two molecular proportions of nitrous acid bodies which may be regarded as para diazo monoalkylphenylnitrosarnins result and that these combine most smoothly and easily with 1.8 dihydroxynaphthalene 3.6 disulfo acid, whether the combination be effected in presence of caustic alkali, sodium carbonate, or sodium acetate. The new coloring-matters so "obtained, which still contain a nitroso group, can be fixed as such on the fiber if dyed from a bath but slightly acidified with acetic acid, the shades produced being violet-red; but if dyed in the usual manner in the presence of mineral acid the nitroso group is split off and blue dyeings result. When these dyes are usedfor dyeing blue shades, it is advantageous to add to the By heating aqueous solutionsof the new nitroso dyestuiis with saponifying agents, such as dilute dilute caustic alkali, the nitroso group is also split off.

The following examples will serve to illustrate the nature of this invention,which, however, isnot confined to the examples:

Emample 1-Pr0d1ttctc'0n of a nitroso colormg matterrdfissolve one hundred and ninety-five parts of monomethyl paraphe'nylenediamin chlorhydrate in two thousand parts of water and three hundred parts ofhydrochloric acid (containing about thirty per cent.'HCl) and while cooling add a solution of one'hundred A and thirty-eight parts ofsodiurn nitrite in Sufidiazomethylphenylnitrosamin is obtained, which is allowed to flow into three hundred and forty-two parts of 1.8,dihydroxynaphthalene 3.6 disulfo-acid monosodium salt, to which about five hundred parts After stirring for about half an hour salt out the-coloring-matter by means of common salt. In a similar mannerthe dyestufi from mono- Example 2 Splitting group.-Dissolve ten parts of the coloringmatter obtained in the previous Example 1 in Our new dyestuffs are characterized by conable reduction a monoalkylparaphenylenediamin body and amido 118 dihydroxynaphthalene 3.6disulfo-acid.

We claim v 1. The process of manufacturing azo dyes nitrosamin with 1. 8' dihydroxynaphthalene 3. 6 disulfo-acid and saponifying the product obtained. f

2. The process of manufacturing azo dyes by combining a para diazomonoalkylphenylnitrosamin with 1. 8 dihydroxynaphthalene 3.;6 disulfo-acid.

3. The process of manufacturing azo dyes by combining para. diazoethylphenylnitrosamin with 1.8 di-hydroxynaphthalene 3.6 di sulfo-acid and "saponifying the product ,obtained. y.

4. The manufacture of azo dyes by combin- KC um 5. The new azo dye which contains a ,ni-

of crystallized sodium acetate'have been added.

ethylparaphenylenediamin can be obtained.

of the nitroso one hundred parts of dilute hydrochloric acid ingpara diazo ethylphenylnitrosamin with 1.8 dihydroxynaphthalene 3 6disu'lfo-acid.

cient water. A'yellow-brown solution of para- 45 a solution of by combining a paradia'zo monoalkylphenyl- 5, taining a nitroso group and yielding on suitjsreso group and on redfiction yields a monoalkyl pefraphen'ylenediamin body and amide 1 .-8;dihydroX-y1'1aphtha1ene 3.6 disulfo-acicl.

6. 'Th" new azo dye which contains a ni- 5 trosog-mup and on reduction yields mono- "ethylparaphenylenediamin and amide 1.8 dihydirekymigihizhalene 3.6 disulfo-acid.

I11 tgeet'imohy whereof We have hereunto set our hands in the presence of two subscribing wltnesses.

PAUL JULIUS. ERNST FUSSENEGGER.

Witnesses: JOHN L. HEINKE, JACOB ADRIAN. 

